Novel quaternary ammonium compounds and process for preparing and using same

ABSTRACT

Novel quaternary ammonium compounds are disclosed, as well as methods for their preparation and their use in the treatment of hair, fibers and textiles as softening and conditioning agents. The high substantivity of these novel quaternary ammonium compounds to hair, fibers, and textiles, and their mildness to the skin and eyes, make them well suited for softening and conditioning fibers for applications such as personal care, laundry, and textile use.  
     For example, quaternary ammonium compounds such as N′,N″,N′″-Triethyl, N′,N′,N′″,N′″-Tetramethyl, N″-[(Polyhydroxypropyl)-ω-hydroxyalkyl], dipropylene triammonium triethosulfate have been prepared. Quaternary ammonium compounds may also include those involving other reactive groups known to those skilled in the art.

BACKGROUND OF THE INVENTION

[0001] 1. Field of the Invention

[0002] The present invention relates to novel quaternary ammoniumcompounds, and more particularly to monomeric polyquaternary ammoniumderivatives of substituted dipropylene triamine, their process ofmanufacture, their use in hair care products and in the treatment offibers and textiles, and preparations containing the quaternary ammoniumcompounds.

[0003] The novel quaternary ammonium compounds of the invention havevery high substantivity to fibers such as wool fiber, acrylic fibers,human hair and textiles made of wool and acrylic fibers or mixed fibers,with excellent conditioning and softening effects. By “mixed fibers” ismeant a combination of polyester and cotton or rayon fibers, orpolyester and wool fibers.

[0004] 2. Description of the Related Art

[0005] Quaternary ammonium compounds are known for a variety ofdifferent applications.

[0006] U.S. Pat. Nos. 2,654,785 and 2,668,854 to Miescher discloseswholly or partially quaternated azalkane diamines. The quaternaryammonium compounds may be used as medication. The patent furtherdiscloses use of diethyl sulfate as a quaternating agent.

[0007] U.S. Pat. No. 4,126,562 to Goffinet et al. discloses non-ionictextile softening compositions comprising a cationic surfactant and anon-ionic fabric-conditioning substance selected from fatty acid estersof mono-or polyhydric alcohols having from 1 to 8 carbon atoms andanhydrides thereof. The composition may additionally comprise aninsoluble cationic softener selected from di-C10-C22 alkyl quaternaryammonium salts and C8-C25 imidazolinium salts.

[0008] U.S. Pat. No. 4,250,112 to Lobach et al. disclosespolyalkylenepolyamines containing quaternary dialkylammonium groups andtheir use as agents for retention of fibers in the manufacture ofpapers.

[0009] U.S. Pat. No. 4,997,912 to Wirtz et al. discloses esters ofoxalkylated alkylalkylenediamines, which may be quaternized, obtained byesterifying oxyalkylated alkylalkylenediamines. The compounds are usedas corrosion inhibitors in crude oil recovery and treatment plants.

[0010] U.S. Pat. No. 4,157,388 to Christiansen discloses polycationic orpolyquaternary ammonium ionenes, which generally are hygroscopic. Thecompounds are useful as conditioning agents for skin, hair and textileproducts.

[0011] U.S. Pat. No. 4,720,383 to Drach et al. discloses imidazoliniumcompounds used for softening and conditioning fibers, hair and skin. Thepatent discloses that it is known to prepare softeners comprisingquaternaries of ethoxylated or nonethoxylated amido amines derived fromthe reaction of high molecular weight acid like stearic and a multiamine such as diethylenetriamine. The standard alkylating agents arediethyl sulfate or dimethyl sulfate.

[0012] U.S. Pat. No. 4,764,306 to Login discloses a process for theproduction of bis-quaternary ammonium compounds comprising contacting atertiary amine with a neutralizing acid, such as HCL, and subsequentlycontacting the resulting mixture with an epoxide, preferablyepihalohydrin or epichlorohydrin. The tertiary amine is preferablystearlyl dimethyl amine or lauryl dimethyl amine. The resultingbis-quaternary ammonium compounds are incorporated into hairconditioners.

[0013] U.S. Pat. No. 4,808,321 to Walley discloses liquid fabricsoftening and antistatic compositions which contain mono-ester analogsof ditallow, dimethyl ammonium chloride.

[0014] U.S. Pat. No. 4,913,828 to Caswell et al. discloses alkylamine-anionic surfactant ion-pair/wax composites useful as fiber, hairand fabric conditioning agents.

[0015] U.S. Pat. Nos. 5,087,733 and 5,206,013 to Deppert et al. disclosesulfur containing quaternary ammonium compounds, and their use as hairconditioning agents.

[0016] U.S. Pat. No. 5,254,271 to Hamann et al. discloses hair andfabric conditioning compositions comprising mixtures of quaternaryammonium compounds with or without ester groups prepared by reactingamines with dimerized fatty acids and subsequent quaternization orprotonation with inorganic or organic acids.

[0017] U.S. Pat. Nos. 5,427,773; 5,427,774; and 5,451,394 to Chaudhuriet al. discloses non-irritating, hair, skin and textile substantive,quaternary ammonium salts of paradialkylamino benzamides. Thesebenzamide derivatives are also active sunscreening agents.

[0018] U.S. Pat. No. 5,863,526 to Yeung et al. discloses a hairconditioning composition comprising homopolymers prepared from ammoniumquaternary salts of amino alkylacrylamides.

[0019] U.S. Pat. No. 5,916,863 to Iacobucci et al. discloses a textilesoftening agent comprising a quaternary ammonium salt which comprises amixture of mono-, di-, and tri-ester components, having high diestercontent and low triester content.

[0020] The references describe the production of cationic and quaternaryammonium compounds and their use in the treatment of hair, fiber andtextiles as softening and conditioning agents. However, none of thereferences disclose or suggest the specific, novel quaternary ammoniumcompounds of the invention, a process of preparing same, or the use ofsuch compounds in the treatment of fibrous materials.

[0021] Additionally, the substantivity characteristics of the quaternaryammonium compounds of the invention are superior to known quaternaryammonium compounds, and are stable in highly acidic or highly alkalinemedium. These properties make the quaternary ammonium compounds of theinvention suitable for use in specialized alkaline fiber or hairtreatment systems such as in hair straightening treatments, at a high pHof 12.00, and also in permanent waving, at a pH of 9-10. The quaternaryammonium compounds of the invention are stable to these extreme pHconditions. The quaternary ammonium compounds of the invention also havevery high substantivity to fibers such as wool fiber, acrylic fibers,human hair and textiles made of wool and acrylic fibers or mixed fibers,with excellent conditioning and softening effects, as shown in Examples52 and 53 below.

OBJECTS AND SUMMARY OF THE INVENTION

[0022] It is an object of the present invention to provide a process forproducing quaternary ammonium compounds which are very mild.

[0023] It is another object of the invention to provide a process formaking quaternary ammonium compounds for use in the treatment of hair,fiber and textile materials.

[0024] It is yet another object of the invention to provide a processfor making quaternary ammonium compounds for use in hair care productsthat allow the use and application of thio-based hair treatmentspecialties and formulations.

[0025] It is a further object of the invention to provide a process formaking quaternary ammonium compounds which have very high substantivityto fibers such as wool fiber, acrylic fibers, human hair, and textilesmade of wool and acrylic fibers or mixed fibers.

[0026] Yet another object of the invention is to provide a method forproducing quaternary ammonium compounds for use in hair shampoo productswhich have excellent conditioning effects when used alone or incombination with other surfactants.

[0027] Another object of the invention is to provide a method ofproducing quaternary ammonium compounds which are stable in highlyacidic or highly alkaline medium.

[0028] It is another object of the invention to provide quaternaryammonium compounds which are excellent conditioners and softeners forfibrous materials.

[0029] Yet another object of the invention is to provide quaternaryammonium compounds which are suitable for use in alkaline fiber or haircare systems such as hair straighteners and permanent wave treatments.

[0030] These and other objects are accomplished by providing a processfor preparing quaternary ammonium compounds, and specifically monomeric,multi-charge, multi-functional quaternary ammonium compounds. Thesequaternary ammonium compounds are improved as compared to commerciallyavailable quaternary ammonium compounds, as they are milder and lessirritating to the skin and eyes. Hair care formulations containing thequaternary ammonium compounds of the invention are conditioning andemollient, have very low toxicological profiles, and are not irritatingto the skin and eyes.

DETAILED DESCRIPTION OF THE INVENTION

[0031] The novel quaternary ammonium compounds of this invention haveunique properties in that they have very high substantivity to fiberssuch as wool fiber, acrylic fibers, human hair and textiles made of wooland acrylic fibers or mixed fibers. Such high substantivity is a usefulproperty for allowing the application of these compounds to fibers, andespecially to human hair. The utility of such compounds in hair careproducts results in excellent conditioning and softening effects. Thehigh substantivity of these novel quaternary ammonium compounds to hair,fibers, and textiles, and their mildness to the skin and eyes, make themwell suited for softening and conditioning fibers for applications suchas personal care, laundry, and textile use.

[0032] The novel quaternary ammonium compounds of the invention arepreferably prepared by:

[0033] 1. Reacting an Amine with alkoxide, preferably Propylene Oxide(“PO”), yielding a polyoxypropylene adduct amine of alkoxide(hereinafter abbreviated “AMP”). The alkoxide is selected from the groupconsisting of propylene oxide, ethylene oxide, and a mixture ofpropylene oxide and ethylene oxide.

[0034] 2. Reacting the adduct AMP of step 1 with a 1,2 epoxyalkanehaving from 3 to 28 carbon atoms (such as ∝-olefin epoxide, i.e.,C₁₆-Epoxide) to produce the hydroxyalkylated condensate;

[0035] 3. Further quaternizing the hydroxyalkylated condensate of step 2with a suitable quaternization agent, preferably diethyl sulfate (“DES”)or dimethyl sulfate (“DMS”), to produce a quaternary ammonium compound.

[0036] 4. Optionally diluting the quaternary ammonium compound producedin Step 3 in water to obtain the desired concentration, preferably a 25%or 50% or 75% solids-liquid solution or dispersion.

[0037] The process of the invention provides a composition of mattercomprising a monomeric polyquaternary ammonium derivative of an amine,preferably a substituted, dipropylene triamine. The preferred, highlysubstituted, dipropylene triamine which is used in the process of theinvention is Tetramethyliminobis-Propylamine, abbreviated herein as“AM”. The propoxylation (or ethoxylation) step adds multiple units ofHydroxypropyl or Hydroxyethyl chains. This propoxylated adduct is thenreacted with of C₁₆-∝-olefin epoxide (preferably one mole) to producethe hydroxyalkylated condensate, i.e.,hydroxycetoxy-polyhydroxypropylated tetramethyliminobis propylamine.This hydroxycetoxy-polyhydroxypropylated tetramethyliminobis propylamineis then further quaternized with 3 moles of Diethyl Sulfate to yield aquaternary of this invention. The preferred molar ratio is 1:2 to 1:3for full quaternization. The preferred molar ratio is 1:3.

[0038] The very mild quaternary ammonium compounds of the invention areparticularly useful in fiber treatment, especially in hair treatmentcompositions that permit the application of thio-based hair treatments,and are suitable for use in alkaline fiber or hair care systems such ashair straighteners and permanent wave treatments. The quaternaryammonium compounds of the invention may be used in shampoos,conditioners, and conditioning shampoos. When the quaternary ammoniumcompounds of the invention are deposited on human hair, they improve theability of the hair to be combed and provide an antistatic effect. Thismakes the hair more manageable.

[0039] The compounds of the present invention are generally semi-liquidsat room temperatures. They mix and dissolve and disperse readily withmost types of shampoo/conditioner formulations.

[0040] The quaternary ammonium compounds of the invention are excellenthair-conditioning agents, as stated above. They are also generalantistats and humectants for fibrous textile products such as rayon andfiber glass, and anti-static agents for textile and rug products ingeneral. The compounds of the invention are also effective as wash cycleconditioners and rewetting agents in some laundry detergentformulations. Thus, the quaternary ammonium compounds of the inventionfind application in compositions such as fabric detergent, shampoos,hair conditioners, and dryer- and washer-added fabric conditioners.

[0041] The foregoing list is only exemplary of the type of compositionsin which the novel quaternary ammonium compounds of this invention maybe used, and, as such, is not to be considered limiting.

[0042] The preferred, highly substituted, dipropylene triamine which isused in the process of the invention is Tetramethyliminobis-Propylamine,abbreviated herein as “AM”, whose structure is:

[0043] The propoxylation (or ethoxylation) step adds multiple units ofHydroxypropyl (or Hydroxyethyl chains) and produces a compound havingthe chemical name Poly(hydroxypropyl) Tetramethyliminobis propylamine,which has the following structure:

[0044] where

[0045] R═H (ethoxylated derivative);

[0046] R═CH₃ (propoxylated derivative); and

[0047] n=1 to 100 moles of Ethylene Oxide (“EO”) and/or Propylene Oxide(“PO”).

[0048] Specifically, it is preferred to form a 3 mole Propoxylate of AM,abbreviated herein as AMP-3, having the chemical name Tri(hydroxypropyl)Tetramethyliminobis propylamine, and having the following structure:

[0049] Alternatively, it is preferred to form a 5 mole Propoxylate ofAM, abbreviated herein as AMP-5, having the chemical namePentahydroxypropyl-Tetramethyliminobis propylamine, which has thefollowing structure:

[0050] This propoxylated adduct is then reacted with a 1,2 epoxyalkanehaving from 3 to 28 carbon atoms, preferably with one mole ofC₁₆-∝-olefin epoxide (abbreviated herein as “C₁₆-Epoxide”), also knownas 1,2-epoxycetane, or 1,2-epoxyhexadecane, which has the followingstructure:

[0051] to produce a hydroxyalkylated condensate, namely, ahydroxycetylalkylated condensate of propxylated or ethoxylatedtetramethyliminobis propylamine, which has the following structure:

[0052] where

[0053] R═H (ethoxylated derivative);

[0054] R═CH₃ (propxylated derivative); and

[0055] n=1 to 100 moles of EO and/or PO.

[0056] Specifically, AMP-3 is reacted with C₁₆-Epoxide to produceTri(hydroxypropyl)-ω-hydroxycetyl-Tetramethyliminobis Propylamine,abbreviated herein as AMP-3-CT. AMP-5 is reacted with C₁₆-Epoxide toproduce Penta(hydroxypropyl)-ω-hydroxycetyl-TetramethyliminobisPropylamine.

[0057] Alternatively, AMP-3 may be reacted with1,2-Epoxydodecane/1,2-Epoxytetradecane to produceTri(hydroxypropyl)-ω-hydroxy(lauryl/myristyl)-Tetramethyliminobispropylamine, abbreviated herein as AMP-3-LM, which has the followingstructure:

[0058] The hydroxyalkoxy-polyhydroxyalkoxylated tetramethyliminobispropylamine is then quaternized with a quaternizing agent, preferably 3moles of Diethyl Sulfate having the formula (C₂H₅)₂SO₄, to yield aquaternary ammonium compound of this invention, having the followinggeneric structure:

[0059] where R₁═CH₃ and/or C₂H₅

[0060] Specifically, the hydroxycetoxy-tri(hydroxypropylated)tetramethyliminobis propylamine is quaternized with Diethyl Sulfatehaving the formula (C₂H₅)₂SO₄, to yield a quaternary ammonium compoundof this invention, having the following structure:

[0061] This quaternary ammonium compound has the trade name FINQUAT®CT-P (INCI Name: Quaternium 89), and the chemical name:N′,N″,N′″-Triethyl, N′,N′,N′″,N′″-Tetramethyl,N″-[(Trihydroxypropyl)-ω-hydroxycetyl], dipropylene triammoniumtriethosulfate.

[0062] Quaternating agents such as alkyl or alkenyl halides, such asmethyl chloride, methyl bromide or methyl iodide, or other dialkylsulfates such as di-methyl sulfate may be used. The molar ratio of thehydroxyalkylated condensate to the quaternating agent is in the range of1:2 to 1:3, with a 1:3 ratio being preferred.

[0063] This invention is also directed to the use of the quaternaryammonium compound produced by the method of the invention in treatinghair, fiber, and textile materials. The quaternary compounds of theinvention are particularly useful in fiber treatment, especially in hairtreatment compositions that permit the application of thio-based hairtreatments.

[0064] More particularly, the compounds of the invention may be obtainedby the following method:

[0065] A. Starting with 1 mole of tetramethyliminobis propylamine.

[0066] B. Adding to the compound of Step A from 1 to 100 moles ofalkoxide, preferably either ethylene oxide or propylene oxide, or amixture of ethylene oxide and propylene oxide, in any ratio.

[0067] C. Reacting each mole of the compound produced in Step B withfrom 0.90 to 1.0 mole of a 1,2 epoxyalkane having from 3 to 28 carbonatoms, preferably C16-∝-olefin-Epoxide.

[0068] D. Quaternizing each mole of the compound produced in Step C with2.5 to 3.00 moles of a suitable quaternization agent, such as diethylsulfate or dimethyl sulfate.

[0069] E. Optionally diluting the quaternary compound produced in Step Din water to obtain the desired concentration, preferably a 25%-75%solids-liquid solution or dispersion, and most preferably a 70%concentration.

[0070] The quaternary ammonium compounds of the invention arepoly-functional with 3 quaternary positions per mole of the molecule.This high density of quaternized nitrogens on the molecule allows themolecule to reach and attach to the anionic hair or fibers. Such anattachment offers antistatic effects besides being beneficial asconditioners and softeners. Furthermore, the feel imparted to hair andfibers/textiles is soft and oil free which is also an advantageousquality of the quaternary ammonium compounds of the invention.

[0071] The quaternary ammonium compounds of this invention may be usedin treatment of hair, textiles and fabrics. The amount used in suchapplications is dependent on the type of compositions, the type andquantity of other ingredients used, and the amount and type offunctional additives that are utilized.

[0072] Further, the quaternary ammonium compounds of this inventionpossess other unusual physio-chemical properties, which can make thembeneficial and unique components of sophisticated treatment systems.Thus, the quaternary ammonium compounds described herein may serve notonly as hair, textile and fiber treatment agents, but may also exhibitone or more other functions, such as adsorption on anionically chargedparticulate matter as in clays, pigments, etc.

[0073] The quaternary ammonium compounds have shown usefulness similarto conventional quaternary ammonium compounds with the additionalbenefits of being mild to the skin. Also, skin feel is even better thanusing conventional quaternary ammonium compounds. In a specificembodiment, and by way of illustration, this invention contemplates theproduction of the following quaternary ammonium compounds:

[0074] 1. Quaternary P3CT, Trade Name: FINQUAT CT-P (INCI Name:Quaternium 89) whose structure is set forth above and whose chemicalname is N′,N″,N′″-Triethyl, N′,N′,N′″,N′″-Tetramethyl,N″-[(Trihydroxypropyl)-ω-hydroxycetyl], dipropylene triammoniumtriethosulfate.

[0075] 2. Quaternary P5CT, chemical name: N′,N″,N′″-Triethyl,N′,N′,N′″,N′″-Tetramethyl, N″-[(Pentahydroxypropyl)-ω-hydroxycetyl],dipropylene triammonium triethosulfate, and whose structure is:

[0076] 3. Quaternary P3LM, chemical name: N,N,N-Triethyl,N′,N′,N′″,N′″-Tetramethyl, N″-[(Trihydroxypropyl)-ω-hydroxypropyl],-ω-hydroxylauryl/myristyl], dipropylene triammonium triethosulfate,whose structure is:

[0077] Some of these quaternary ammonium compounds are used in hair careformulations. Hair care formulations prepared according to theinvention, which contain the quaternary ammonium compounds addedthereto, can be formed, without limitation, into applications such assolutions, emulsions, gels, solids, emulsions, aerosols, powders,creams, granules, or tablets.

[0078] Mildness and emolliency of these quaternary ammonium compounds isof importance to the improved hair care products including thequaternary ammonium compounds of the invention. One major aspect ofquaternary ammonium compounds of this invention is their very, very lowto negligible toxicological effects indicating their mildness in haircare products.

[0079] Thus, the advantages of the quaternary ammonium compounds of theinvention include:

[0080] Mildness of the formulations containing the quaternary ammoniumcompounds

[0081] Very low toxicological profile

[0082] Low irritation

[0083] Impart softer feel and better control of fibers

[0084] Thus, the novel quaternary ammonium compounds of this inventionhave unique properties in that they are mild to the skin, have very lowto negligible toxicological effects, and very low eye and skinirritation. These properties make these quaternary ammonium compoundsuseful as vehicles or carriers, dispersants, emulsifiers, emollients,solubilizers and conditioners for hair care formulations such as haircreams, lotions, as well as other formulations. The foregoing list isonly exemplary of the type of compositions in which the quaternaryammonium compounds of this invention may be used, and, as such, is notto be considered limiting.

[0085] The amount of such quaternary ammonium compounds to be used insuch compositions is dependent on the type of hair care compositions,the desired dosage or amount of active ingredient to be delivered, thetype and quantity of other ingredients, such as cosmetic ingredientsused, the amount and type of functional additives that are utilized, theuser's skin and hair type, and the severity and extent of the skin orhair condition, and other parameters that will be apparent to thoseskilled in the art. Generally, compositions containing the quaternaryammonium compounds of the invention are topically applied in effectiveamounts to the affected areas of the skin or to hair. Typically, theamount of quaternary ammonium compounds used ranges from about 0.5% to10.0%, by weight, of the formulation.

[0086] The quaternary ammonium compounds of the invention haveproperties such as, being less greasy, less oily, low toxicity, ease ofemulsification, acid and alkaline stability, the ability to form gelswith suspending agents, water solubility/dispersibility, and the abilityto be combined with many common hair care ingredients.

[0087] The following are non-limiting examples of processes forpreparing the quaternary ammonium compounds compositions of theinvention (Examples 1 to 51), comparative substantivity properties(Example 52), comparative conditioning properties (Example 53), andtoxicology studies (Example 54). In the Examples, as well as throughoutthis application, the chemical and scientific symbols have theircustomary meanings and all percents are weight percents unless otherwisespecified.

[0088] Example Nos. 1 through 51 identify quaternary ammonium compoundsproduced by the process of the invention. For ease of identification,each preparation is identified by both an Example Number and a ReferenceNo., where applicable.

[0089] Although the Examples use only selected compounds andformulations, it should be understood that the examples are illustrativeand not limited. Thus, any of the aforementioned Reactants A and B maybe substituted according to the teachings of this invention in thefollowing Examples. TABLE I Abbreviations for Examples AM =Tetramethyliminobis Propylamine E = Ethylene Oxide P = Propylene OxideAME3 = 3 moles Ethoxylate of AM AME5 = 5 moles Ethoxylate of AM AMP-3 =3 moles Propoxylate of AM AMP-5 = 5 moles Propoxylate of AM AMP3-CT =C16 Epoxide condensate of AMP3 AMP5-CT = C16 Epoxide condensate of AMP5AMP3LM = C12-14 Epoxide Condensate of AMP-3 DES = Diethyl Sulfate QuatP3CT = DES Quaternary of AMP3CT Quat P5CT = DES Quaternary of AMP5CTQuat P3LM = DES Quaternary of AMP3LM

EXAMPLE 1 (REF. NO. 117-158-A) Preparation of AMP-3 (3 Mole Propoxylateof AM)

[0090] 10 moles, i.e., 1890 gms. of AM were reacted under nitrogen with30 moles, i.e., 1740 gms. propylene oxide in a stainless steel reactorof 5 liter capacity. The reaction was kept at 120° C.-130° C. and 50-60psi. Reaction was held there until exotherm subsided. The mass waschecked for amine value before propoxylation and after propoxylation.The amine value before propoxylation was 890 mg KOH/g and amine valueafter propoxylation was 460 mg KOH/g, which compared well with thetheoretical value of 464 mg KOH/g. The reactor was then cooled andbrought to atmospheric pressure. The yield was 3630 gms. of amberliquid.

EXAMPLE 2 (REF. NO. 117-158-B) Preparation of AMP-5 (5 Mole Propoxylateof AM)

[0091] 7 moles, i.e., 1323 gms. of AM was reacted under nitrogen with 35moles, i.e., 2030 gms. propylene oxide in a stainless steel reactor of 5liter size. The reaction temperature was kept at 120° C.-130° C. and50-60 psi. Reaction was held there until exotherm subsided. The mass waschecked for amine value before propoxylation and after propoxylation.The amine value before propoxylation was 890 mg KOH/g and amine valueafter propoxylation was 355 mg KOH/g, which compared well with thetheoretical value of 351 mg KOH/g. The reactor was then cooled andbrought to atmospheric pressure. The yield was 3353 gms. of amberliquid.

EXAMPLE 3 (REF. NO. 117-158-C) Large Batch Preparation of AMP-3 (3 MolePropoxylate of AM)

[0092] 5246 lbs. of AM was charged to an evacuated stainless steelreactor under nitrogen atmosphere. To this was added, in portions, 4839lbs. of propylene oxide. Addition was done such that heat input andexotherm brought the temperature to 120° C.-130° C. and pressure of50-60 psi. Reaction was held there until exotherm subsided and additionof propylene oxide was completed. The reaction mass was checked afterpropoxylation for amine value, which came to 460 mg KOH/g. The aminevalue before propoxylation was 890 mg KOH/g. The amine value of 460 mgKOH/g compared well with the theoretical value of 464 mg KOH/g. Thereactor was then cooled and brought to atmospheric pressure. The yieldin the reactor was 10,085 lbs.

EXAMPLE 4 (118-298) Preparation of AMP3CT (Cl6 Epoxide Condensate ofAMP3)

[0093] In 1 liter four neck reaction flask with stirrer, condenser, andthermometer was charged 309.7 grams of Example #1, i.e. AMP3. Nitrogenflow was maintained throughout. To this was added 190.3 grams ofC16-a-Olefin Epoxide. The initial alkalinity of this mixture was 281 mgKOH/g. The temperature was raised to 150° C. with continued nitrogenatmosphere. Reaction was continued at 150° C. for the duration of 2hours. The alkalinity remained constant indicating that there was noloss of amine equivalence. The reaction mass was a dark amber liquid.Upon cooling to 30° C. the yield was 497 grams.

EXAMPLE 5 (118-302) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0094] In a one liter four neck glass reaction flask was added 287.5grams of AMP-3CT from Example #4 (ref. 118-298). The inert atmosphere ofnitrogen was maintained throughout. Temperature was raised to 55° C. atwhich time addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was212.5 gr. of which the first portion was 47.23 gr. The balance of DESwas added in units of 35.41 gr. at temperature of 100° C.-104° C. Eachportion was reacted for 30 minutes before the next portion of DES wasadded. Alkalinity and pH were checked the in-process sample. Alkalinitywas 22 mg KOH/g and pH of 25% water solution was 5.8. Additionalquantity of 17 gr. DES was added and reacted for 30 min. Alkalinity wasnone and pH 25% solution in water was <1.0. Reaction was cooled to 80°C. Added 71 gr. of 1,3-butylene glycol and the mass was mixed for 1 hr.at 80° C. The mixture was then cooled to 30° C. The yield of 587 gramswas obtained as semisolid paste. This is abbreviated as Quat P3CT.

EXAMPLE 6 (118-304) Preparation of Aqueous Quat P3CT

[0095] In a 500 ml glass reaction flask was added 75 gr. of the productof Ex.#5 (Anhydrous Quat-P3CT) and 225 gr. of water. Mixture wassubjected to mixing and pH adjustments with a 25% sodium hydroxidesolution. The pH was brought to 5.9. Mixture was brought to 80° C. undernitrogen. It was then subjected to a reduced pressure of 15″-20″ Hg. andheld there for one hour. 32 grams of the distillate was collected. Added32 grams of water to the reaction flask and equalized the pressure to 1atmosphere. Cooled to 30° C. The yield of this mixture was 300 grams inthe form of fluid dispersion.

EXAMPLE 7 (121-18) Preparation of AMP3CT (Cl6 Epoxide Condensate ofAMP3)

[0096] In 1 liter four neck reaction flask with stirrer, condenser, andthermometer was charged 309.7 grams of example #1 i.e. AMP3. Nitrogenflow was maintained throughout. To this was added 190.3 grams ofC16-∂-Olefin Epoxide. The initial alkalinity of this mixture was 281 mgKOH/g. The temperature was raised to 150° C. with continued nitrogenatmosphere. Reaction was continued at 150° C. for the duration of 2hours. The alkalinity remained constant indicating that there was noloss of amine equivalence. The reaction mass was a dark amber liquid.Upon cooling to 30° C. the yield was 498 grams.

EXAMPLE 8 (121-21) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0097] In a 1 liter four neck glass reaction flask was added 287.5 gramsof AMP-3CT from Ex.#7 (ref. 121-18). The inert atmosphere of nitrogenwas maintained throughout. Temperature was raised to 55° C. at whichtime the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was212.5 grams of which the first portion was 47.23 grams. The balance ofDES was added in units of 35.41 grams at temperature of 100° C.-104° C.Each portion was reacted for 30 minutes before the next portion of DESwas added. Alkalinity and pH were checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH of 25%. Water solution was 5.8.Additional quantity of 22 grams of DES was added and reacted for 30minutes. Alkalinity was none and pH 25%. Solution in water was <1.0.Reaction was cooled to 80° C. and added 71 grams of 1,3-butylene glycoland the mass was mixed for 1 hour at 80° C. The mixture was then cooledto 30° C. The yield of 597 grams was obtained as a semisolid paste. Thisis abbreviated as Quat P3CT.

EXAMPLE 9 (121-24) Preparation of Aqueous Quat P3CT

[0098] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #8 (i.e. Anhydrous Quat P3CT) and 225 grams of water.Mixture was subjected to mixing and pH adjustment with a 25% w/w sodiumhydroxide solution. The pH was brought to 5.9. Mixture was brought to80° C. under nitrogen. It was then subjected to a reduced pressure of15″-20″ Hg. and held there for 1 hour. 60 grams of the distillate wascollected. Added 60 grams of water to the reaction flask and equalizedthe pressure to 1 atmosphere. Cooled to 30° C. The yield of this mixturewas 300 grams in the form of a fluid dispersion.

EXAMPLE 10 (121-41A) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0099] In a 500 ml four neck glass reaction flask was added 172.5 gramsof AMP3CT from Ex.#7 (ref. 121-18). The inert atmosphere of nitrogen wasmaintained throughout. Temperature was raised to 55° C. at which timethe addition of DES (diethyl sulfate) was started so that the exothermcame to approximately 85° C.-104° C. Total quantity of DES was 127.5grams of which the first portion was 34.77 grams. The balance of DES wasadded in units of 11.60 grams at temperature of 100° C.-104° C. Eachportion was reacted for 30 minutes before the next portion of DES wasadded. Alkalinity and pH was checked on the in-process sample.Alkalinity was 20 mg KOH/g and pH of 25% water solution was 5.95.Reaction was cooled to 80° C. The yield of 300 grams was obtained assolid paste. This is abbreviated as Quat P3CT.

EXAMPLE 11 (121-44) Preparation of Aqueous Quat P3CT

[0100] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #10 (121-41A) (i.e. Anhydrous Quat P3CT) and 225grams of water. Mixture was subjected to mixing and without pHadjustment. Mixture was brought to 80° C. under nitrogen. It was thensubjected to a reduced pressure of 15″-20″ Hg. Hg and held there for 1hour. 22 grams of the distillate were collected. Added 22 gms. of thewater to the reaction flask and equalized the pressure to 1 atmosphere.Cooled to 30° C. The yield of this mixture was 300 gms. in the form of afluid dispersion.

EXAMPLE 12 (121-25) Preparation of AMP3CT (Cl6 Epoxide Condensate ofAMP3)

[0101] In 1 liter four neck reaction flask with stirrer, condenser, andthermometer was charged 309.7 grams of example #1 i.e. AMP3. Nitrogenflow was maintained throughout. To this was added 190.3 gr. ofC16-∝-Olefin Epoxide. The initial alkalinity of this mixture was 283 mgKOH/g. The temp. was raised to 150° C. with continued nitrogenatmosphere. Reaction was continued at 150° C. for the duration of 2 hrs.The alkalinity remained constant indicating there was no loss of amineequivalence. The reaction mass was a dark amber liquid. Upon cooling to30° C. the yield was 498 grs.

EXAMPLE 13 (121-26) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0102] In a 1 liter four neck glass reaction flask was added 287.5 gr.of AMP-3CT from Ex.#12 (ref. 121-25). The inert atmosphere of nitrogenwas maintained throughout. Temperature was raised to 55° C. at whichtime the addition of DES(diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was212.5 grams of which the first portion was 47.23 gr. The balance of DESwas added in units of 34.71 gr. at temperature of 100° C.-104° C. Eachportion was reacted for 30 min. before the next portion of DES wasadded. Alkalinity and pH was checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH of 25% water solution was 5.8.Additional quantity of 32 gr. of DES was added and reacted for 30minutes. Alkalinity was none and pH 25% solution in water was <1.0.Reaction was cooled to 80° C. Added 71 gr. of 1,3-butylene glycol andthe mass was mixed for 1 hr. at 80° C. The mixture was then cooled to30° C. The yield of 609 grams was obtained as a semisolid paste. This isabbreviated as Quat P3CT.

EXAMPLE 14 (121-28) Preparation of Aqueous Quat P3CT

[0103] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #1 3 (i.e. anhydrous Quat P3CT) and 225 grams ofwater. Mixture was subjected to mixing and pH adjustments with a 25% w/wsodium hydroxide solution. The pH was brought to 5.9. Mixture wasbrought to 80° C. under nitrogen. It was then subjected to a reducedpressure of 15″-20″ Hg. and held there for 1 hour. 32 grams ofdistillate were collected. Added 32 grams of water to the reaction flaskand equalized the pressure to 1 atmosphere. Cooled to 30° C. The yieldof this mixture was 300 grams in the form of a fluid dispersion.

EXAMPLE 15 (121-31) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0104] In a 500 ml four neck glass reaction flask was added 172.5 gramsof AMP-3CT from Ex.#12 (ref. 121-25). The inert atmosphere of nitrogenwas maintained throughout. Temperature was raised to 55° C. at whichtime the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was127.5 grams of which the first portion was 22.4 gr. The balance of DESwas added in units of 17.92 gr. at temperature of 100° C.-104° C. Eachportion was reacted for 30 min. before the next portion of DES wasadded. Alkalinity and pH was checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH of 25% water solution was 5.8.Additional quantity of 10 gr. DES was added and reacted for 30 minutes.Alkalinity was none and pH 25% solution in water was <1.0. Reaction wascooled to 80° C. Added 42 grams of 1,3-butylene glycol and the mass wasmixed for 1 hour at 80° C. The mixture was then cooled to 30° C. Theyield of 350 grams was obtained was a semisolid paste. This isabbreviated as Quat P3CT.

EXAMPLE 16 (121-32) Preparation of Aqueous Quat P3CT

[0105] In a 500 ml glass reaction flask was added 75 gms. of the productof example #15 (i.e. anhydrous Quat P3CT) and 225 gms. of water. Mixturewas subjected to mixing and pH adjustments with a 25% w/w sodiumhydroxide solution. The pH was brought to 5.9. Mixture was brought to80° C. under nitrogen. It was then subjected to a reduced pressure of15″-20″ Hg. and held there for 1 hour. 21 grams of the distillate wascollected. Added 21 grams of water to the reaction flask and equalizedthe pressure to 1 atmosphere. Cooled to 30° C. The yield of this mixturewas 300 grams in the form of a fluid dispersion.

EXAMPLE 17 (121-38) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0106] In a 500 ml four neck glass reaction flask was added 172.5 gr. ofAMP-3CT from Ex.#4 (ref. 118-298). The inert atmosphere of nitrogen wasmaintained throughout. Temperature was raised to 55° C. at which timethe addition of DES (diethyl sulfate) was started so that the exothermcame to approximately 85° C.-104° C. Total quantity of DES was 127.5grams of which the first portion was 22.4 grams. The balance of DES wasadded in units of 17.92 grams at temperature of 100° C.-104° C. Eachportion was reacted for 30 minutes before the next portion of DES wasadded. Alkalinity and pH were checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH of 25% water solution was 5.8.Additional quantity of 7.5 grams DES was added and reacted for 30minutes. Alkalinity was none and pH 25% solution in water was <1.0.Reaction was cooled to 80° C. Added 42.6 grams of 1,3-butylene glycoland the mass was mixed for 1 hour at 80° C. The mixture was then cooledto 30° C. The yield of 351 grams was obtained as a semi-fluid paste.This is abbreviated as Quat P3CT.

EXAMPLE 18 (121-40) Preparation of Aqueous Quat P3CT

[0107] In a 500 ml glass reaction flask was added 75 gms. of the productof example #17 (i.e. anhydrous Quat P3CT) and 225 gms. of water. Mixturewas subjected to mixing and pH adjustments with a 25% w/w sodiumhydroxide solution. The pH was brought to 5.9. Mixture was brought to80° C. under nitrogen. It was then subjected to a reduced pressure of15″-20″ Hg. and held there for 1 hour. 26 grams of the distillate wascollected. Added 26 grams of water to the reaction flask and equalizedthe pressure to 1 atmosphere. Cooled to 30° C. The yield of this mixturewas 300 grams in the form of a fluid dispersion.

EXAMPLE 19 (121-41) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0108] In a 500 ml four neck glass reaction flask was added 172.5 gramsof AMP-3CT from example #7 (reference 121-18). The inert atmosphere ofnitrogen was maintained throughout. Temperature was raised to 55° C. atwhich time the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was127.5 grams of which the first portion was 22.4 grams. The balance ofDES was added in units of 17.92 grams at temperature of 100° C.-104° C.Each portion was reacted for 30 minutes before the next portion of DESwas added. Alkalinity and pH was checked on the in-process samples.Alkalinity was 22 mg KOH/g and pH of 25% water solution was 5.8.Reaction was cooled to 80° C. Added 42 grams of 1,3-butylene glycol andthe mass was mixed for 1 hour at 80° C. The mixture was then cooled to30° C. The yield of 342 grams was obtained as a semi-fluid paste. Thisis abbreviated as Quat P3CT.

EXAMPLE 20 (121-45) Preparation of Aqueous Quat P3CT

[0109] In a 500 ml glass reaction flask was added 75 gms. of the productof example #19 (i.e. anhydrous Quat P3CT) and 225 gms. of water. Mixturewas brought to 80° C. under nitrogen. It was then subjected to a reducedpressure of 15″-20″ Hg and held there for 1 hour. 24 grams of thedistillate was collected. Added 24 grs. of water to the reaction flaskand equalized the pressure to 1 atmosphere. Cooled to 30° C. The yieldof this mixture was 300 grams in the form of a fluid dispersion.

EXAMPLE 21 (121-46) Preparation of AMP3CT (Cl6 Epoxide Condensate ofAMP3)

[0110] In 1 liter four neck reaction flask with stirrer, condenser, andthermometer was charged 309.7 grams example #1, i.e., AMP3. Nitrogenflow was maintained throughout. To this was added 190.3 grams ofC16-∝-Olefin Epoxide. The initial alkalinity of this mixture was 286 mgKOH/g. The temperature was raised to 150° C. with continued nitrogenatmosphere. Reaction was continued at 150° C. for the duration of 2hours. The alkalinity remained constant indicating that there was noloss of amine equivalence. The reaction mass was a dark amber liquid.Upon cooling to 30° C. the yield was 498 grams.

EXAMPLE 22 (121-47A) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0111] In a 1 liter four neck glass reaction flask was added 287.5 gramsof AMP-3CT from example #21 (reference 121-46). The inert atmosphere ofnitrogen was maintained throughout. Temperature was raised to 55° C. atwhich time the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was170.0 grams of which the first portion was 36 grams. The balance of DESwas added in units of 24 grams at temperature of 100° C.-104° C. Eachportion was reacted for 30 minutes before the next portion of DES wasadded. Alkalinity and pH was checked on the in-process sample.Alkalinity was 20 mg KOH/g and pH of 25% water solution was 5.95.Reaction was cooled to 80° C. The yield of 480 grams was obtained as asolid paste. This is abbreviated as Quat P3CT.

EXAMPLE 23 (121-49) Preparation of Aqueous Quat P3CT

[0112] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #22 (i.e. anhydrous Quat P3CT) and 225 gms. of water.Mixture was brought to 80° C. under nitrogen. It was then subjected to areduced pressure of 15″-20″ Hg and held there for 1 hour. 31 grams ofthe distillate was collected. Added 31 grams of water to the reactionflask and equalized the pressure to 1 atmosphere. Cooled to 30° C. Theyield of this mixture was 300 grams in the form of a fluid dispersion.

EXAMPLE 24 (121-47) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0113] In a 1 liter four neck glass reaction flask was added 287.5 gramsof AMP-3CT from Ex.#21 (ref. 121-46). The inert atmosphere of nitrogenwas maintained throughout. Temperature was raised to 55° C. at whichtime the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was170.0 grams of which the first portion was 36 grams. The balance of DESwas added in units of 24 grams at temperature of 100° C.-104° C. Eachportion was reacted for 30 minutes before the next portion of DES wasadded. Alkalinity and pH were checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH 25% solution in water was 5.8.Reaction was cooled to 80° C. Add 72 grams of 1,3 butylene glycol andthe mass was mixed for 1 hour at 80° C. The mixture was then cooled to30° C. The yield of 550 grams was obtained as a semi-solid paste. Thisis abbreviated as Quat P3CT.

EXAMPLE 25 (121-50) Preparation of Aqueous Quat P3CT

[0114] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #24 (i.e. anhydrous Quat P3CT) and 225 gms. of water.Mixture was brought to 80° C. under nitrogen. It was then subjected to areduced pressure of 15″-20″ Hg and held there for 1 hour. 31 grams ofthe distillate was collected. Added 31 grams of water to the reactionflask and equalized the pressure to 1 atmosphere. Cooled to 30° C. Theyield of this mixture was 300 grams in the form of a fluid dispersion.

EXAMPLE 26 (121-151A) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0115] In a 500 ml four neck glass reaction flask was added 172.5 gramsof AMP-3CT from Ex.#21 (ref. 121-46). The inert atmosphere of nitrogenwas maintained throughout. Temperature was raised to 55° C. at whichtime the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was127.5 grams of which the first portion was 22.4 grams. The balance ofDES was added in units of 17.92 grams at temperature of 100° C.-104° C.Each portion was reacted for 30 minutes before the next portion of DESwas added. Alkalinity and pH were checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH of 25% water solution was 5.8.Additional quantity of 7 grams DES was added and reacted for 30 minutes.Alkalinity was none and pH 25% solution in water <1.0. Reaction wascooled to 80° C. The yield of 305 grams was obtained as a solid paste.This is abbreviated as Quat P3CT.

EXAMPLE 27 (121-53) Preparation of Aqueous Quat P3CT

[0116] In a 500 ml glass reaction flask was added 75 grams of theproduct of Ex.#26 (i.e. anhydrous Quat P3CT) and 225 gms. of water.Mixture was subjected to mixing and pH adjustment with a 25% w/w sodiumhydroxide solution. The pH was brought to 5.9. Mixture was brought to80° C. under nitrogen. It was then subjected to a reduced pressure of15″-20″ Hg and held there for 1 hour. Added 26 grams of water to thereaction flask and equalized the pressure to 1 atmosphere. Cooled to 30°C. The yield of this mixture was 300 grams in the form of a fluiddispersion.

EXAMPLE 28 (121-51) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0117] In a 500 ml four neck glass reaction flask was added 172.5 grs.of AMP-3CT from Ex. #21 (ref. #121-46). The inert atmosphere of nitrogenwas maintained throughout. Temperature was raised to 55° C. at whichtime the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was127.5 grams of which the first portion was 22.4 grams. The balance ofDES was added in units of 17.92 grams at temperature of 100° C.-104° C.Each portion was reacted for 30 minutes before the next portion of DESwas added. Alkalinity and pH were checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH of 25% water solution was 5.8.Additional quantity of 7 grams DES was added and reacted for 30 minutes.Alkalinity was none and pH 25% solution in water was <1.0. Reaction wascooled to 80° C. Added 42 grams of 1,3-butylene glycol and the mass wasmixed for 1 hour at 80° C. The mixture was then cooled to 30° C. Theyield of 345 grams was obtained as a semisolid paste. This isabbreviated as Quat P3CT.

EXAMPLE 29 (121-54) Preparation of Aqueous Quat P3CT

[0118] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #28 (i.e. anhydrous Quat of P3CT) and 225 gms. ofwater. Mixture was subjected to mixing and pH adjustment with a 25% w/wsodium hydroxide solution. The pH was brought to 5.9. Mixture wasbrought to 80° C. under nitrogen. It was then subjected to a reducedpressure of 15″-20″ Hg and held there for 1 hour. 22 grams of thedistillate was collected. Added 22 grams of water to the reaction flaskand equalized the pressure to 1 atmosphere. Cooled to 30° C. The yieldof this mixture was 300 grams in the form of a fluid dispersion.

EXAMPLE 30 (121-57) Preparation of AMP3CT (Cl6 Epoxide Condensate ofAMP3)

[0119] In 500 ml. four neck reaction flask with stirrer, condenser, andthermometer was charged 185.82 grams example #1, i.e., AMP3. Nitrogenflow was maintained throughout. To this was added 114.18 grams ofC16-∝-Olefin Epoxide. The initial alkalinity of this mixture was 282 mgKOH/g. The temperature was raised to 150° C. with continued nitrogenatmosphere. Reaction was continued at 150° C. for the duration of 2hours. The alkalinity remained constant indicating that there was noloss of amine equivalence. The reaction mass was a dark amber liquid.Upon cooling to 30° C. the yield was 300 grams.

EXAMPLE 31 (121-60A) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0120] In a 500 ml four neck glass reaction flask was added 172.5 gramsof AMP3CT from example #30 (reference 121-57). The inert atmosphere ofnitrogen was maintained throughout. Temperature was raised to 55° C. atwhich time the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was127.5 grams of which the first portion was 22.4 grams. The balance ofDES was added in units of 17.92 grams at temperature of 100° C.-104° C.Each portion was reacted for 30 minutes before the next portion of DESwas added. Alkalinity and pH were checked on the in-process sample.Alkalinity was 20 mg KOH/g and pH of 25% water solution was 5.95.Reaction was cooled to 80° C. The yield of 300 grams was obtained assolid paste. This is abbreviated as Quat P3CT.

EXAMPLE 32 (121-62) Preparation of Aqueous Quat P3CT

[0121] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #31 (i.e. anhydrous Quat P3CT) and 225 grams ofwater. Mixture was brought to 80° C. under nitrogen. It was thensubjected to a reduced pressure of 15″-20″ Hg and held there for 1 hour.18 grams of the distillate were collected. Added 18 grams of water tothe reaction flask and equalized the pressure to 1 atmosphere. Cooled to30° C. The yield of this mixture was 300 grams in the form of a fluiddispersion.

EXAMPLE 33 (121-60B) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0122] In a 500 ml four neck glass reaction flask was added 172.5 gramsof AMP3CT from Ex.#30 (ref. 121-57). The inert atmosphere of nitrogenwas maintained throughout. Temperature was raised to 55° C. at whichtime the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was127.5 grams of which the first portion was 22.4 grams. The balance ofDES was added in the units of 17.92 grams at temperature of 100° C.-104°C. Each portion was reacted for 30 minutes before the next portion ofDES was added. Alkalinity and pH were checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH of 25% water solution was 5.8.Reaction was cooled to 80° C. Added 42.6 grams of 1,3-butylene glycoland the mass was mixed for 1 hour at 80° C. The mixture was then cooledto 30° C. The yield of 340 grams was obtained as a semi-fluid paste.This is abbreviated as Quat P3CT.

EXAMPLE 34 (121-63) Preparation of Aqueous Quat P3CT

[0123] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #33 (i.e. anhydrous Quat P3CT) and 225 grams ofwater. Mixture was brought to 80° C. under nitrogen. It was thensubjected to a reduced pressure of 15″-20″ Hg and held there for 1 hour.20 grams of the distillate were collected. Added 20 grams of water tothe reaction flask and equalized the pressure to 1 atmosphere. Cooled to30° C. The yield of this mixture was 300 grams in the form of a fluiddispersion.

EXAMPLE 35 (121-59) Preparation of AMP3CT (Cl6 Epoxide Condensate ofAMP3)

[0124] In 500 ml reaction flask with stirrer, condenser, and thermometerwas charged 185.82 grams example #1, i.e., AMP3. Nitrogen flow wasmaintained throughout. To this was added 114.18 gms. of C16-∂-OlefinEpoxide. The initial alkalinity of this mixture was 282 mg KOH/g. Thetemperature was raised to 150° C. with continued nitrogen atmosphere.Reaction was continued at 150° C. for the duration of 2 hours. Thealkalinity remained constant indicating that there was no loss of amineequivalence. The reaction mass was a dark amber liquid. Upon cooling to30° C. the yield was 300 gms.

EXAMPLE 36 (121-64A) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0125] In 500 ml four neck glass reaction flask was added 172.5 grams ofAMP-3CT from example #35 (reference 121-59). The inert atmosphere ofnitrogen was maintained throughout. Temperature was raised to 55° C. atwhich time the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was127.5 gms. of which the first portion was 22.4 grams. The balance of DESwas added in units of 17.92 grams at temperature of 100° C.-104° C. Eachportion was reacted for 30 minutes before the next portion of DES wasadded. Alkalinity and pH were checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH of 25% water solution was 5.8.Additional quantity of 15 grams DES was added and reacted for 30minutes. Alkalinity was none and pH 25% solution in water <1.0. Reactionwas cooled to 80° C. The yield of 315 grams was obtained as a solidpaste. This is abbreviated as Quat P3CT.

EXAMPLE 37 (121-66) Preparation of Aqueous Quat P3CT

[0126] In 500 ml four neck reaction flask was added 75 gms. of theproduct of example #36 (i.e. anhydrous Quat P3CT) and 225 grams ofwater. Mixture was subjected to mixing and pH adjustments with a 25%sodium hydroxide solution. The pH was brought to 5.9. Mixture wasbrought to 80° C. under nitrogen. It was then subjected to a reducedpressure of 15″-20″ Hg. and held there for 1 hour. 40 grams ofdistillate were collected. Added 40 grams of water to the reaction flaskand equalized the pressure to 1 atmosphere. Cooled to 30° C. The yieldof this mixture was 300 gms. in the form of a fluid dispersion.

EXAMPLE 38 (121-64) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0127] In a 500 ml four neck reaction flask was added 172.5 grams ofAMP-3CT from example #35 (reference #121-59). The inert atmosphere ofnitrogen was maintained throughout. Temperature was raised to 55° C. atwhich time the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was127.5 grams of which the first portion was 22.4 grams. The balance ofDES was added in units of 17.92 grams at temperature of 100° C.-104° C.Each portion was reacted for 30 minutes before the next portion of DESwas added. Alkalinity and pH were checked on the in-process sample.Alkalinity was 22 mg KOH/g and pH of 25% water solution was 5.8.Additional quantity of 15 grams DES was added and reacted for 30minutes. Alkalinity was none and pH 25% solution in water was <1.0.Reaction was cooled to 80° C. Added 42 grams of 1,3-butylene glycol andthe mass was mixed for 1 hour at 80° C. The mixture was then cooled to30° C. The yield of 355 grams was obtained as a semisolid paste. This isabbreviated as Quat P3CT.

EXAMPLE 39 (121-67) Preparation of Aqueous Quat P3CT

[0128] In a 500 ml glass reaction flask was added 75 gms. of the productof Ex.#38 (i.e. anhydrous Quat P3CT) and 225 grams of water. Mixture wassubjected to mixing and pH adjustment with a 25% w/w sodium hydroxidesolution. The pH was brought to 5.9. Mixture was brought to 80° C. undernitrogen. It was then subjected to a reduced pressure of 15″-20″ Hg. andheld there for 1 hour. 36 grams of distillate were collected. Added 36grams of water to the reaction flask and equalized the pressure to 1atmosphere. Cooled to 30° C. The yield of this mixture was 300 grams inthe form of a fluid dispersion.

EXAMPLE 40 (118-299) Preparation of AMP5CT (Cl6 Epoxide Condensate ofAMP5)

[0129] In 1 liter four neck reaction flask with stirrer, condenser, andthermometer was charged 339 grams example #2, i.e., AMP5. Nitrogen flowwas maintained throughout. To this was added 161 grams of C16-∝-OlefinEpoxide. The initial alkalinity of this mixture was 239.89 mg KOH/g. Thetemperature was raised to 150° C. with continued nitrogen atmosphere.Reaction was continued at 150° C. for the duration of 2 hours. Thealkalinity remained constant indicating that there was no loss of amineequivalence. The reaction mass was a dark amber liquid. Upon cooling to30° C. the yield was 499 grams.

EXAMPLE 41 (118-305) Preparation of Quat P5CT (DES Quat of AMP5CT)

[0130] In a 1 liter four neck glass reaction flask was added 306.7 grs.of AMP-5CT from Ex.#40 (ref. #118-299). The inert atmosphere of nitrogenwas maintained throughout. Temperature was raised to 55° C. at whichtime the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was193.3 grams of which the first portion was 36.24 grams. The balance ofDES was added in units of 24.16 at temperature of 100° C.-104 C. Eachportion was reacted for 30 minutes before the next portion of DES wasadded. Alkalinity and pH were checked on the in-process sample.Alkalinity was 18 mg KOH/g and pH of 25% water solution was 4.4.Additional quantity of 15 grams DES was added and reacted for 30minutes. Alkalinity was none and pH 25% solution in water was <1.0.Reaction was cooled to 80° C. Added 70 grams of 1,3-butylene glycol andthe mass was mixed for 1 hour at 80° C. The mixture was then cooled to30° C. The yield of 585 grams was obtained as a semisolid paste. This isabbreviated as Quat P5CT.

EXAMPLE 42 (118-308) Preparation of Aqueous Quat P5CT

[0131] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #41 (i.e. anhydrous Quat P5CT) and 225 grams ofwater. Mixture was subjected to mixing and pH adjustments with a 25% w/wsodium hydroxide solution. The pH was brought to 5.7. Mixture wasbrought to 80° C. under nitrogen. It was then subjected to a reducedpressure of 15″-20″ Hg and held there for 1 hour. 30 grams of distillatewere collected. Added 30 grams of water to the reaction flask andequalized the pressure to 1 atmosphere. Cooled to 30° C. The yield ofthis mixture was 300 grams in the form of a fluid dispersion.

EXAMPLE 43 (117-75)

[0132] Preparation of AMP3CT (Cl6 Epoxide Condensate of AMP3)

[0133] In 1 liter four neck reaction flask with stirrer, condenser, andthermometer was charged 434 gr. Ex.#1, i.e., AMP3. Nitrogen flow wasmaintained throughout. To this was added 266 gr. of C16-∂-OlefinEpoxide. The initial alkalinity of this mixture was 280.22 mg KOH/g. Thetemperature was raised to 150° C. with continued nitrogen atmosphere.Reaction was continued at 150° C. for the duration of 2 hrs. Thealkalinity remained constant indicating there was no loss of amineequivalence. The reaction mass was a dark amber liquid. Upon cooling to30° C. the yield was 700 grs.

EXAMPLE 44 (117-79) Preparation of Quat P3CT (DES Quat of AMP3CT)

[0134] In a 1 liter four neck glass reaction flask was added 402.50grams of AMP-3CT from Ex.#43 (ref. 117-75). The inert atmosphere ofnitrogen was maintained throughout. Temperature was raised to 55° C. atwhich time the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was297.50 grams of which the first portion was 75 grams. The balance of DESwas added in units of 42 grs. at temperature of 100° C.-104° C. Eachportion was reacted for 30 min. before the next portion of DES wasadded. Alkalinity and pH were checked on the in-process samples.Alkalinity was 6.23 mg KOH/g and pH of 25% water solution was 3.5.Reaction was cooled to 80° C. Added 100 grams 1,3-butylene glycol andthe mass was mixed for 1 hour at 80° C. The mixture was then cooled to30° C. The yield of 795 grams was obtained as a semisolid paste. This isabbreviated as Quat P3CT.

EXAMPLE 45 (118-292) Preparation of Aqueous Quat P3CT

[0135] In a 500 ml glass reaction flask was added 75 grams of theproduct of example #44 (i.e. anhydrous Quat P3CT) and 225 grams ofwater. Mixture was subjected to mixing and pH adjustments with a 25% w/wsodium hydroxide solution. The pH was brought to 5.9. Mixture wasbrought to 80° C. under nitrogen. It was then subjected to a reducedpressure of 15″-20″ Hg. and held there for 1 hour. 30 grams of thedistillate were collected. Added 30 grams of water to the reaction flaskand equalized the pressure to 1 atmosphere. Cooled to 30° C. The yieldof this mixture was 300 grams in the form of a fluid dispersion.

EXAMPLE 46 (117-77) Preparation of AMP5CT (Cl6 Epoxide Condensate ofAMP5)

[0136] In 1 liter four neck reaction flask with stirrer, condenser, andthermometer was charged 474.60 grams of example #2, i.e., AMP5. Nitrogenflow was maintained throughout. To this was added 225.40 grams ofC16-∝-Olefin Epoxide. The initial alkalinity was 230 mg KOH/g. Thetemperature was raised to 150° C. with continued nitrogen atmosphere.Reaction was continued at 150° C. for the duration of 2 hours. Thealkalinity remained constant indicating that there was no loss of amineequivalence. The reaction mass was a dark amber liquid. Upon cooling to30° C. the yield was 700 grams.

EXAMPLE 47 (117-81) Preparation of Quat P5CT (DES Quat of AMP5CT)

[0137] In a 1 liter four neck glass reaction flask was added 429.38grams of AMP-5CT from example #46 (reference 117-77). The inertatmosphere of nitrogen was maintained throughout. Temperature was raisedto 55° C. at which time the addition of DES (diethyl sulfate) wasstarted so that the exotherm came to approximately 85° C.-104° C. Totalquantity of DES was 270.62 grams of which the first portion was 70grams. The balance of DES was added in units of 30 grams at temperatureof 100° C.-104° C. Each portion was reacted for 30 minutes before thenext portion of DES was added. Alkalinity and pH were checked on thein-process sample. Alkalinity was 4.93 mg KOH/g and pH of 25% watersolution was 3.8. Reaction was cooled to 800 C. Added 100 grams of1,3-butylene glycol and the mass was mixed for 1 hour at 80° C. Themixture was then cooled to 30° C. The yield of 795 grams was obtained asa semisolid paste. This is abbreviated as Quat P3CT.

EXAMPLE 48 (118-293) Preparation of Aqueous Quat P5CT

[0138] In a 500 ml glass reaction flask was added 75 grams of theproduct of Ex. #47 (i.e. anhydrous Quat P5CT) and 225 gr. of water.Mixture was subjected to mixing and pH adjustments with a 25% w/w sodiumhydroxide solution. The pH was brought to 5.9. Mixture was brought to80° C. under nitrogen. It was then subjected to a reduced pressure of15″-20″ Hg and held there for 1 hour. 36 gr. of the distillate werecollected. Added 36 gr. of water to the reaction flask and equalized thepressure to 1 atmosphere. Cooled to 30° C. The yield of this mixture was300 grams in the form of a fluid dispersion.

EXAMPLE 49 (121-95) Preparation of AMP3LM (Cl2-Cl4 Epoxide Condensate ofAMP3)

[0139] In 500 ml four neck reaction flask with stirrer, condenser, andthermometer was charged 167.5 grams of example #1, i.e., AMP3. Nitrogenflow was maintained throughout. To this was added 82.5 grams ofC12-C14-∝-Olefin Epoxide (70:30). The initial alkalinity of this mixturewas 296 mg KOH/g. The temperature was raised to 150° C. with continuednitrogen atmosphere. Reaction was continued at 150° C. for the durationof 2 hours. The alkalinity remained constant indicating that there wasno loss of amine equivalence. The reaction mass was a dark amber liquid.Upon cooling to 30° C. the yield was 250 grams.

EXAMPLE 50 (121-96) Preparation of Quat P3LM (DES Quat of AMP3LM)

[0140] In a 500 ml four neck glass reaction flask was added 137.37 gramsof AMP3LM from Ex. #49 (ref. 121.95). The inert atmosphere of nitrogenwas maintained throughout. Temperature was raised to 55° C. at whichtime the addition of DES (diethyl sulfate) was started so that theexotherm came to approximately 85° C.-104° C. Total quantity of DES was112.62 grams of which the first portion was 35.57 grams. The balance ofDES was added in units of 23.71 gr. at temperature of 100° C.-104° C.Each portion was reacted for 30 minutes before the next portion of DESwas added. Alkalinity and pH were checked on the in-process sample.Alkalinity was none and pH 25% solution in water was 1.2. Reaction wascooled to 80° C. Added 35 grams of 1,3-butylene glycol and the mass wasmixed for 1 hour at 80° C. The mixture was then cooled to 30° C. Theyield of 280 gams was obtained as a semisolid paste. This is abbreviatedas Quat P3LM.

EXAMPLE 51 (121-98) Preparation of Aqueous Quat P3LM

[0141] In 1 500 ml glass reaction flask was added 75 grams of theproduct of example #50 (i.e. anhydrous Quat P3LM) and 225 grams ofwater. Mixture was subjected to mixing and pH adjustments with a 25% w/wsodium hydroxide solution. The pH was brought to 5.9. Mixture wasbrought to 80° C. under nitrogen. It was then subjected to a reducedpressure of 15″-20″ Hg and held there for 1 hour. 30 grams of thedistillate were collected. Added 30 grams of water to the reaction flaskand equalized the pressure to 1 atmosphere. Cooled to 30° C. The yieldof this mixture was 300 grams in the form of a fluid dispersion.

EXAMPLE 52 Comparative Substantivity Properties

[0142] Substantivity is defined as the ability of the quaternary (orcationic) substance to be attracted to an anionic surface such as hairand wool. Substantivity is taken as a conditioning efficacy parameterfor hair care products. In the industry, the Rubine Dye Uptake Test istypically performed to screen for the property of substantivity.

[0143] A control fabric swatch of wool is treated in water without anytreatment with a quaternary compound. The test articles, i.e., fabricswatches, are applied with a certain level of “activity” to the sameweight fabric swatches as the control swatch. The treated fabricswatches are rinsed and then further treated in a solution of anionicacid dye such as Rubine Red Dye. The treatment with dye solution allowsthe fabric to attract the strong anionic dye solution with the help of aquaternary compound that has been applied to the swatch. The depth ofcolor is stronger or weaker depending upon the substantivity (higher orlower) of the quaternary. The deeper the color, the greater thesubstantivity of the quaternary.

[0144] The Rubine Dye Uptake Test was performed using the followingmaterials: 1. Wool (Worsted) Swatches: Size = 3½ inches × 5½ inchesWeight = 2.6 gm. 2. Dye Solution: 0.50 gms. Dye (Direct Red #207, i.e.,Lumicrease Bordeaux 3LR, Clariant, Inc., Charlottte, North Carolina.0.125 gms. Glacial Acetic Acid q.s. Water 1000 mls. 3. Dye Solution forTest Swatch: 150 mls. for each swatch 4. Test Sample QuaternarySolution: 0.5% Active Quaternary in Water i.e., 1.0 gm. of ActiveQuaternary in 200 ml. Water

[0145] Procedure:

[0146] The control swatch is treated in water without quaternarycompound. Separate swatches for each quaternary substance are treatedfor 5 minutes with mild stirring in separate beakers. The swatches arethen individually (separately) rinsed with water.

[0147] The control swatch and treated swatches are further treated (eachone in a separate beaker) with dye solution for 5 minutes and rinsed intap water at 40° C. The swatches are allowed to air dry.

[0148] The depth of the dye uptake is compared. The higher the colordepth, the higher the substantivity of the quaternary.

[0149] The results of the test are set forth in Table II below, where asubstantivity rating of 1 is the best, and a rating of 10 is poor. TABLEII Comparative Substantivity Properties TEST ARTICLES % ACTIVEQUATERNARY INCI NAME RATINGS No Conditioner None — 10 (Control)FINQUAT ® CT¹ 0.50 Quaternium 75 3 FINQUAT ® CT-P² 0.50 Quaternium 39 1Product of Invention Example #6, 9, 20) Stearalkonium 0.50Steraralkonium 2 Chloride Chloride (Stearyl Trimethyl Ammonium Chloride)Cetyl Trimethyl 0.50 Cetrimonium Chloride 2 Ammonium ChlorideDimethyldiallyl 0.50 Poly Quaternium 7 2 Ammonium Chloride³Dimethyldiallyl 1.78 Poly Quaternium 7 2 Ammonium Chloride³

[0150] As can be seen in Table II, FINQUAT® CT-P (the product ofExamples #6, 9 and 20) shows superior substantivity in this group ofquaternaries tested. This is indicative of high substantivity for itsuse as a conditioning agent for hair care products. Hair is similar towool fibers. Accordingly, wool is used as a sample textile material,serving a dual purpose in testing quaternaries.

EXAMPLE 53

[0151] Comparative Conditioning Properties

[0152] Conditioning efficacy is judged by evaluating wet and dry combcharacteristics and flyaway features of the hair tresses treated withthe conditioners.

[0153] A comparative study was done using the quaternary of thisinvention (Product of Example #6, 9, 20) known commercially as FINQUAT®CT-P, as compared to other commercially marketed products.

[0154] A prototype formulation of Conditioner Base was made as shownbelow: Water: Q.S. to 100 Parts Hydroxyethyl Cellulose: 0.40 PartsPropylene GlycolL: 10.00 Parts PEG-75 Lanolin: 0.25 Parts Conditioner:Q.S. for 2.5% Actives

[0155] Procedure:

[0156] Mix hydroxy ethyl cellulose in water. Dissolve completely at 50°C. Add propylene glycol and PEG-75 lanolin. Add conditioner and mixwell. Cool to 25° C.

[0157] Conditioners Used in the Study:

[0158] 1. Control (without any conditioner)

[0159] 2. FINQUAT® CT (INCI Name: Quaternium 75)

[0160] 3. FINQUAT® CT-P (INCI Name: Quaternium 89)

[0161] (Product of Invention Example Nos. 6, 9, and 20, as in Table II)

[0162] 4. Stearyl dimethyl ammonium chloride

[0163] INCI Name: Stearalkonium Chloride, the most widely used hairconditioner ingredient)

[0164] 5. Cetyl trimethyl ammonium chloride

[0165] (INCI Name: Cetrimonium Chloride)

[0166] 6. Dimethyldiallyl ammonium chloride

[0167] (INCI Name: Poly Quaternium 7)

[0168] The attached table gives the results of the test of comparativeconditional properties, with a rating of 1 being the best, and a ratingof 10 being poor. TABLE III Comparative Conditioning Properties WET DRYFLYAWAY COMB COMB (INCHES) Control (No conditioner) 8 5 3 FINQUAT ® CT¹6 2 2.5 (Quaternium-75) FINQUAT ® CT-P² 2 1 2 (Quaternium-89) (Productof Example #6, 9, 20) Stearalkonium Chloride 5 4 4.5 (Stearyl TrimethylAmmonium Chloride) Cetrimonium Chloride 7 3 4.0 Dimethyldiallyl 7 4 4.0Ammonium Chloride³ (Polyquaternium 7)

[0169] As can be seen in Table III, FINQUAT® CT-P (the product ofExamples #6, 9 and 20) shows superior conditioning properties in thisgroup of quaternaries tested. This is indicative of its benefits for useas a conditioning agent for hair care products.

EXAMPLE 54

[0170] Toxicology Studies

[0171] Toxicology studies compared the new quaternary ammonium compoundof the invention (hereinafter referred by its tradename FINQUAT® CT-P)to FINQUAT® CT, available from Finetex, Inc. of Elmwood Part, N.J. Thestudies indicate that the new quaternary ammonium compound of theinvention, FINQUAT® CT-P, is milder than FINQUAT® CT, which itself is amild quaternary.

[0172] Both products were tested at 3.0% active for dermal and ocularirritation by in-vitro Mat Tek Protocols (Skin model and Ocular Tissuemodel).

[0173] Construction of a Dose Response Curve: The extractant solutionwithin each well was pipetted up and down several times to insure thateach is well mixed. 200 microliters of each of the mixed extractionsolutions was then pipetted into separate wells of a 96 well microtiterplate. A Dynatech MR 4000 Automatic Microplate Reader was used todetermine the optical density of each extract at 570 nm. With theabsorbance of a negative control defined as 100%, the percentabsorbencies of the articles were determined (% viability=100×(OD[article]/OD [negative control]). The calculated percentages directlycorrelate with the cell metabolism in the EpiOcular samples.

[0174] Using a semi-log scale, the percent viability (liner “y” axis)was plotted versus the dosing time (log “x” axis). By interpolation, thetime at which the viability has dropped to 50% was determined.

[0175] Correlation of In Vitro and In Vivo Results: (Epi-Ocular) Thefollowing equation was used to estimate the rabbit Draize eye score: LogDraize=2.067−(0.979×Lot ET-50(min)). Based on the literature (Kay, J. H.and Calandra, J. C., “Interpretation of Eye Irritation Tests,” J. Soc.Cosmetic Chem., 13, 281-289 (1962), the ocular irritancy can becategorized into the following groups based on the Draize score: DraizeIrritancy Epiocular Score Classification Example ET-50 (min). 0-15Non-irritating, P53-75 Lanolin, Tween 20 >240-20.5 Minimal 15.1-25 Mild2% Sodium Dodecyl Sulfate <20.5-9.67 25.1-50 Moderate 5% Triton X-100<9.67-3.48 50.1-110 Severe, 5% Benzalkonium Chloride <3.48 Extreme

[0176] Correlation of In vitro and In vivo results: (EpiDerm) Thefollowing groupings were used in assigning expected in vivo irritancyresponses based upon the Et-50 results obtained using the EpiDerm: ET-50(hrs) Expected In vivo Irritancy Example <0.5 Severe, probably corrosiveConc. Nitric Acid 0.5-4 Moderate 1% Sodium Dodecyl Sulfate 4-12 Moderateto mild 1% Triton X-100 12-24 Very mild Baby Shampoo 24 Non-irritating10% Tween 20

[0177] The results are:

[0178] Ocular Results/Classification

[0179] FINQUAT® CT=Minimal Irritancy (as in Tween)

[0180] FINQUAT® CT-P=Non-Irritancy (as in Peg 75 Lanolin)

[0181] Positive Control=Mild Irritancy

[0182] Triton X-100 0.3%

[0183] Dermal Results/Classification

[0184] FINQUAT® CT=Very mild range

[0185] FINQUAT® CT-P=Non-Irritating range

[0186] Positive Control=Moderate to mild range

[0187] Triton X-100 0.3%

[0188] It will be understood that the embodiments described herein aremerely exemplary and that a person skilled in the art may make manyvariations and modifications without departing from the spirit and scopeof the invention. For example, the invention is not intended to bestrictly limited to the named reactants and catalysts, recited pHranges, reaction temperatures, reaction conversion, or other parameters.Rather, the invention as claimed extends to many possible variations notspecifically detailed. All such variations and modifications areintended to be included in the scope of the invention as describedherein.

We claim:
 1. A quaternary ammonium compound represented by the followingstructure:

where R₁═CH₃ and/or C₂H₅

X═C₂H₅SO₄ OR CH₃SO₄
 2. A quaternary ammonium compound represented by thefollowing structure:

and having the INCI name Quaternium 89, the tradename FINQUAT® CT-P, andthe chemical name N′,N″,N′″-Triethyl, N′,N′,N′″,N′″-Tetramethyl,N″-[(Trihydroxypropyl)-ω-hydroxycetyl], dipropylene triammoniumtriethosulfate.
 3. A quaternary ammonium compound represented by thefollowing structure:

and having the chemical name N′,N″,N′″-Triethyl, N′,N′, N′″,N′″-Tetramethyl,N″-[(Pentahydroxypropyl)-ω-hydroxycetyl], dipropylenetriammonium triethosulfate, and known herein as Quaternary P5CT.
 4. Aquaternary ammonium compound represented by the following structure:

and having the chemical name N,N,N-Triethyl, N′,N′,N′″,N′″-Tetramethyl,N″-[(Trihydroxypropyl)-ω-hydroxypropyl], -ω-hydroxylauryl/myristyl],dipropylene, triammonium triethosulfate and knonw herein as QuaternaryP3LM.
 5. The quaternary ammonium compound of claim 1 formed by reactingdiethyl sulfate and hydroxycetylalkylated condensate of propxylated orethoxylated tetramethyliminobis propylamine represented by the followingstructure:

where R═H (ethoxylated derivative); R═CH₃ (propxylated derivative); andn=1 to 100 moles of EO and/or PO;
 6. Poly(hydroxypropylated)tetramethylminobis propylamine having the structure:

where R═H (ethoxylated derivative); R═CH₃ (propoxylated derivative); andn=1 to 100 moles of Ethylene Oxide and/or Propylene Oxide
 7. Thepoly(hydroxypropylated) tetramethylminobis propylamine of claim 6wherein n is preferably 3 moles of propylene oxide.
 8. Thepoly(hydroxypropylated) tetramethylminobis propylamine of claim 6wherein n is preferably 5 moles of propylene oxide. 9.Hydroxy(lauryl/myristyl)oxy polyhydroxypropylated tetramethylminobispropylamine having the structure:


10. A process for preparing the quaternary ammonium compound of claim 1,comprising: (a) reacting a substituted, dipropylene triamine withalkoxide to produce a polyoxypropylene adduct amine of alkoxide; (b)reacting the adduct of step (a) with a 1,2 epoxyalkane having from 3 to28 carbon atoms to produce a hydroxyalkoxy-polyhydroxyalkoxylatedtetramethyliminobis propylamine; (c) quaternizing each mole of thehydroxyalkoxy-polyhydroxyalkoxylated tetramethyliminobis propylamine ofstep (b) with a quaternizing agent to yield a quaternary ammoniumcompound having the following structure:

where R₁═CH₃ and/or C₂H₅

X═C₂H₅SO₄ OR CH₃SO₄
 11. The process of claim 10 wherein the substituted,dipropylene triamine of step (a) preferably comprisesTetramethyliminobis-Propylamine.
 12. The process of claim 10 whereinsaid alkoxide of step (a) is selected from the group consisting ofpropylene oxide, ethylene oxide, and a mixture of ethylene oxide andpropylene oxide.
 13. The process of claim 10 wherein the 1,2 epoxyalkaneof step (b) preferably comprises C₁₆-∝-olefin epoxide.
 14. The processof claim 10 wherein said quaternizing agent of step (c) is selected fromthe group consisting of diethyl sulfate, dimethyl sulfate, methylchloride, methyl bromide and methyl iodide.
 15. The process of claim 10wherein after step (c), the step of diluting the quaternary ammoniumcompound produced in step (c) in water to obtain the desiredconcentration.
 16. The process of claim 15, wherein the preferredconcentration is in the range of 25% to 75% solids-liquid solution ordispersion.
 17. The process of claim 10 wherein 1 mole of a substituted,dipropylene triamine is reacted with 3 moles of propylene oxide.
 18. Theprocess of claim 10 wherein 1 mole of a substituted, dipropylenetriamine is reacted with 5 moles of propylene oxide.
 19. The process ofclaim 10 wherein said hydroxyalkoxy-polyhydroxyalkoxylatedtetramethyliminobis propylamine is preferablyhydroxycetoxy-polyhydroxypropylated tetramethyliminobis propylamine. 20.The process of claim 10 wherein saidhydroxyalkoxy-polyhydroxyalkoxylated tetramethyliminobis propylamine ispreferably hydroxy(lauryl/myristyl)oxy-polyhydroxypropylatedtetramethyliminobis propylamine.
 21. A fiber conditioning compositioncomprising a conditioning effective amount of at least one quaternaryammonium compound as defined in claim
 1. 22. A cosmetic hair careformulation comprising at least one quaternary ammonium compound asdefined in claim
 1. 23. A softening, conditioning and antistaticcomposition for hair, fibers, and textiles, comprising: (a) a carrier;and dispersed therein, (b) a softening, conditioning and antistaticeffective amount of at least one of the quaternary ammonium compoundsrepresented by the general formula of claim
 1. 24. The composition ofclaim 23 further comprising one or more components selected from thegroup consisting of surfactants, neutralizers, stabilizers, coloringagents, fragrances, plasticizers, foam stabilizers, film formingpolymers, preservatives, antistats, sequestrants, water, dyes, perfume,thickeners, preservatives, plant extracts, and customary additive andauxiliary substances.
 25. The composition of claim 23 wherein saidquaternary ammonium compound comprises at least from 0.5% to 10% byweight of said composition.
 26. A method for softening and conditioninghair, fibers, or textiles comprising applying to said hair, fibers, ortextiles for a sufficient time a softening and conditioning effectiveamount of at least one of the quaternary ammonium compounds representedby the general formula of claim 1.